1-(4-Fluorobenzyl)-4-(nitromethyl)piperidin-2-one → 4-(Aminomethyl)-1-(4-fluorobenzyl)piperidin-2-one

HRID 1436868Notes

Reaction equation

HRID 1436868 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][N+:14]([O-])=O)[CH2:9][C:8]2=[O:17])=[CH:4][CH:3]=1>C(O)C.[Ni].O>[NH2:14][CH2:13][CH:10]1[CH2:11][CH2:12][N:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:19][CH:18]=2)[C:8](=[O:17])[CH2:9]1

Participants

5

Reactant 1

HCID 690699721-(4-Fluorobenzyl)-4-(nitromethyl)piperidin-2-one

Product 1

HCID 690679234-(Aminomethyl)-1-(4-fluorobenzyl)piperidin-2-one

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a degassed solution of 1-(4-fluorobenzyl)-4-(nitromethyl)piperidin-2-one (1.4 g, 5.3 mmol) in absolute ethanol (80 mL) was added wet Raney nickel catalyst (1.4 g of a 50% weight slurry in water) which was washed to neutral pH with deionized water and absolute ethanol. The reaction mixture was shaken under an atmosphere of 55 psi of hydrogen for 16 hours. The product mixture was filtered through celite and the filtrate was concentrated under vacuum to afford the title compound as colorless viscous oil. 1H NMR (400 MHz, CDCl3) δ 7.24 (m, 2H), 7.01 (t, J=8.7 Hz, 2H), 4.64 (d, J=14.6 Hz, 1H), 4.44 (d, 1H), 3.23 (m, 2H), 2.65 (m, 2H), 2.16-1.28 (m).

Workup

  1. washwas washed to neutral pH with deionized water and absolute ethanol
  2. filtrationThe product mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-b3eb453890aa4608b08f0f319793f107
Source dataset
uspto-grants-2009_11
Patent number
US07619086B2

Reaction notes

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